Sleeps up to 16
Ideal for large families, reunions & groups.
Discover the perfect getaway with our spacious vacation rentals on Hilton Head Island, accommodating up to 16 guests. Ideal for large families, reunions, or group vacations, these properties offer ample space, luxurious amenities, and stunning locations. Enjoy fully-equipped kitchens, multiple living areas, numerous bedrooms, and private pools. Pair these amenities with our signature Luxury Concierge services, and you can rest assured that your vacation will be relaxing and memorable.
Situated close to the island's beautiful beaches, golf courses, tennis & pickleball courts and outdoor activities, our rentals ensure a memorable stay for everyone. Book your Hilton Head Island vacation rental today and experience unparalleled comfort and convenience for your entire group in this picturesque coastal paradise!
26 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
6 Gunnery is a spacious and inviting home ideally located in the heart of Sea Pines. Nestled halfway between Harbour Town and South Beach Marina, this property offers the perfect combination of convenience and tranquility. Enjoy an easy 10-minute walk or 5-mi
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
With beautiful craftsmanship throughout the well-appointed house. The ground level has a newly refinished pine floor and an open-plan design, with the large kitchen overlooking the cozy living room equipped with a comfortable sleeper sofa. There are lots of b
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning rental home offers a picturesque and convenient location, perfect for creating unforgettable vacation memories. This two-story retreat is designed for groups, with a private pool, a huge outdoor dining table, and five bedrooms with multiple bunk
THIS HOME IS A SMOKE-FREE HOME AND IS RESERVED FOR NON-SMOKERS ONLY (THIS INCLUDES RENTERS AND ANY GUESTS).
SMOKING IS STRICTLY PROHIBITED ANYWHERE IN OR ON THIS OCEANFRONT PROPERTY, BOTH INDOOR AND OUTDOORS. SMOKING, VAPING, OR THE USE OF ANY TOBACCO PRODUCTS IS PROHIBITED ANYWHERE IN OR ON THE PROPERTY.
NO PETS / ANIMALS ALLOWED (THIS INCLUDE
19 Armada
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunning Palmetto Dunes beach home has recently undergone a full renovation, boasting 5 bedrooms and offering a short stroll to both the beach and the Robert Trent Jones Golf Course. The highlight of this retreat is the brand new private pool, perfect fo
13 Sea Lane
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Views, views, and more views! What better way to start your day than listening to the surf, enjoying the beautiful scenery of the marsh with active wildlife, and the ocean just beyond while sipping your coffee on the deck? An expansive, gorgeous beach is just
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled in the charming Burke\'s Beach on Hilton Head Island, this remarkable 6-bedroom, 5 1/2-bathroom home is a coastal paradise that offers a luxurious and comfortable lifestyle. As you step inside, you\'ll be greeted by a spacious and well-designed interi
1 Sandy Beach Trail
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax.
This amazing villa featu
1013 Seacrest
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Nestled along the scenic fairways of the renowned Atlantic Dunes Golf Course, this brand new 6-bedroom, 6-bath home in Sea Pines captures the essence of upscale coastal living. 169 North Sea Pines welcomes you with a blend of contemporary design and Southern
169 North Sea Pines Drive
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This breath-taking 4th-row home is one of a kind and has everything you need and more for your next Hilton Head vacation. The great room is spacious and is sure to keep guests feeling right at home with its stylish but cozy furnishings! Soaring ceilings and h
6 Grey Widgeon
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.
The first floor features a very open floor plan that offers easy access between the multiple living
2 Royal Tern
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This oceanfront home sits in the prestigious Palmetto Dunes Resort and offers panoramic ocean views from every angle.
The great room, kitchen, and dining area make up the great room of the home; the extremely open floor plan allows for an easy flow and plent
10 Ketch
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